CA2856711A1 - Novel heterocyclic alkanol-derivatives - Google Patents
Novel heterocyclic alkanol-derivatives Download PDFInfo
- Publication number
- CA2856711A1 CA2856711A1 CA2856711A CA2856711A CA2856711A1 CA 2856711 A1 CA2856711 A1 CA 2856711A1 CA 2856711 A CA2856711 A CA 2856711A CA 2856711 A CA2856711 A CA 2856711A CA 2856711 A1 CA2856711 A1 CA 2856711A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- plants
- optionally substituted
- halogen
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 19
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 4
- -1 1,3-dioxetan-2-yl Chemical group 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 86
- 230000008569 process Effects 0.000 claims description 53
- 241000233866 Fungi Species 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 230000009261 transgenic effect Effects 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 230000003032 phytopathogenic effect Effects 0.000 claims description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical class [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 197
- 239000000463 material Substances 0.000 abstract description 13
- 244000005700 microbiome Species 0.000 abstract description 13
- 241000607479 Yersinia pestis Species 0.000 abstract description 7
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- 239000002904 solvent Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 235000018102 proteins Nutrition 0.000 description 37
- 102000004169 proteins and genes Human genes 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 28
- 238000009472 formulation Methods 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- 239000008346 aqueous phase Substances 0.000 description 22
- 230000000749 insecticidal effect Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000003630 growth substance Substances 0.000 description 21
- 241000238631 Hexapoda Species 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 239000003995 emulsifying agent Substances 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 201000010099 disease Diseases 0.000 description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
- 235000013399 edible fruits Nutrition 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 235000017168 chlorine Nutrition 0.000 description 18
- 229940060038 chlorine Drugs 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 230000001681 protective effect Effects 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 16
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 16
- 239000004009 herbicide Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 230000009466 transformation Effects 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000003306 harvesting Methods 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 241000193388 Bacillus thuringiensis Species 0.000 description 12
- 229940097012 bacillus thuringiensis Drugs 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000010353 genetic engineering Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229920000151 polyglycol Polymers 0.000 description 11
- 239000010695 polyglycol Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- 241000219146 Gossypium Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 230000002068 genetic effect Effects 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 240000002791 Brassica napus Species 0.000 description 9
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- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
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- 239000003086 colorant Substances 0.000 description 8
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
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- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 7
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11190684 | 2011-11-25 | ||
| EP11190684.8 | 2011-11-25 | ||
| PCT/EP2012/073426 WO2013076227A1 (de) | 2011-11-25 | 2012-11-23 | Neue heterocyclische alkanol-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2856711A1 true CA2856711A1 (en) | 2013-05-30 |
Family
ID=47216311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2856711A Abandoned CA2856711A1 (en) | 2011-11-25 | 2012-11-23 | Novel heterocyclic alkanol-derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9198429B2 (ru) |
| EP (1) | EP2782904A1 (ru) |
| JP (1) | JP2015502933A (ru) |
| KR (1) | KR20140098164A (ru) |
| CN (1) | CN104066725A (ru) |
| AR (1) | AR088981A1 (ru) |
| BR (1) | BR112014012588A2 (ru) |
| CA (1) | CA2856711A1 (ru) |
| CO (1) | CO6970612A2 (ru) |
| EA (1) | EA201491031A1 (ru) |
| IN (1) | IN2014CN03823A (ru) |
| MX (1) | MX2014006073A (ru) |
| TW (1) | TW201328599A (ru) |
| WO (1) | WO2013076227A1 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170132743A (ko) * | 2015-04-02 | 2017-12-04 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 농약 및 식물 성장 조절제로서의 트리아졸 유도체 |
| WO2016156311A1 (en) * | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Triazole derivatives as pesticides and plant growth regulators |
| WO2018050535A1 (en) | 2016-09-13 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| UY37416A (es) | 2016-09-29 | 2018-04-30 | Bayer Ag | Nuevos derivados de triazol |
| WO2018060076A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| CN114195734A (zh) * | 2021-12-27 | 2022-03-18 | 天象生物药业邢台有限责任公司 | 一种5-甲基-2-氨基噻唑的合成方法 |
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| DE3220730A1 (de) | 1982-06-02 | 1983-12-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,2-dimethyl-3-aryl-cyclopropan-carbonsaeuren (carbonsaeureestern), neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| US4610716A (en) | 1982-12-14 | 1986-09-09 | Ciba-Geigy Corporation | Fluorinated azolyl ethanol growth regulators and microbicides |
| DE3311702A1 (de) | 1983-03-30 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, verfahren zu ihrer herstellung und deren verwendung |
| DE3315808A1 (de) * | 1983-04-30 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Antivirale mittel |
| DE3535456A1 (de) | 1984-11-02 | 1986-05-15 | Bayer Ag, 5090 Leverkusen | Antimykotische mittel |
| CN1008735B (zh) | 1984-11-02 | 1990-07-11 | 拜尔公司 | 以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物 |
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| DE3627071A1 (de) | 1986-08-09 | 1988-02-11 | Bayer Ag | Substituierte hydroxypropylamin-derivate |
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| FR2734842B1 (fr) | 1995-06-02 | 1998-02-27 | Rhone Poulenc Agrochimie | Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un gene de l'hydroxy-phenyl pyruvate dioxygenase, tolerantes a certains herbicides |
| US5773704A (en) | 1996-04-29 | 1998-06-30 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Herbicide resistant rice |
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| FR2772789B1 (fr) | 1997-12-24 | 2000-11-24 | Rhone Poulenc Agrochimie | Procede de preparation enzymatique d'homogentisate |
| DE19821614A1 (de) | 1998-05-14 | 1999-11-18 | Hoechst Schering Agrevo Gmbh | Sulfonylharnstoff-tolerante Zuckerrübenmutanten |
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| US6768044B1 (en) | 2000-05-10 | 2004-07-27 | Bayer Cropscience Sa | Chimeric hydroxyl-phenyl pyruvate dioxygenase, DNA sequence and method for obtaining plants containing such a gene, with herbicide tolerance |
| US6660690B2 (en) | 2000-10-06 | 2003-12-09 | Monsanto Technology, L.L.C. | Seed treatment with combinations of insecticides |
| FR2815969B1 (fr) | 2000-10-30 | 2004-12-10 | Aventis Cropscience Sa | Plantes tolerantes aux herbicides par contournement de voie metabolique |
| JP2004528821A (ja) | 2000-12-07 | 2004-09-24 | シンジェンタ リミテッド | 除草剤抵抗性植物 |
| US20020134012A1 (en) | 2001-03-21 | 2002-09-26 | Monsanto Technology, L.L.C. | Method of controlling the release of agricultural active ingredients from treated plant seeds |
| FR2844142B1 (fr) | 2002-09-11 | 2007-08-17 | Bayer Cropscience Sa | Plantes transformees a biosynthese de prenylquinones amelioree |
| JP2004359646A (ja) * | 2003-06-09 | 2004-12-24 | Ss Pharmaceut Co Ltd | 抗真菌活性を有する新規アゾール誘導体 |
| JP2006279419A (ja) | 2005-03-29 | 2006-10-12 | Sanyo Electric Co Ltd | チャンネル切替制御方法、コマーシャル終了通知方法、およびテレビ放送受信装置 |
| NZ566028A (en) | 2005-08-31 | 2011-09-30 | Monsanto Technology Llc | Nucleotide sequences encoding insecticidal proteins |
| US20070214515A1 (en) | 2006-03-09 | 2007-09-13 | E.I.Du Pont De Nemours And Company | Polynucleotide encoding a maize herbicide resistance gene and methods for use |
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| CN105368799A (zh) | 2008-04-14 | 2016-03-02 | 拜耳作物科学公司 | 新的突变羟基苯基丙酮酸双加氧酶，dna序列和耐受hppd抑制剂除草剂的植物分离 |
| EP2177496A1 (en) | 2008-10-07 | 2010-04-21 | Assistance Publique - Hopitaux de Paris | New analogs of polysphorin and uses thereof for treating or preventing malaria |
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| CN102958923A (zh) * | 2010-05-27 | 2013-03-06 | 拜耳知识产权有限责任公司 | 新型杂环链烷醇衍生物 |
| JP5872548B2 (ja) * | 2010-05-27 | 2016-03-01 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺菌剤としてのヘテロ環式アルカノール誘導体 |
| CN102947282B (zh) * | 2010-05-27 | 2016-06-01 | 拜耳知识产权有限责任公司 | 作为杀真菌剂的杂环链烷醇衍生物 |
| CN102985414B (zh) * | 2010-05-27 | 2016-05-18 | 拜耳知识产权有限责任公司 | 作为杀真菌剂的杂环硫代取代链烷醇衍生物 |
-
2012
- 2012-11-23 CA CA2856711A patent/CA2856711A1/en not_active Abandoned
- 2012-11-23 BR BR112014012588A patent/BR112014012588A2/pt not_active IP Right Cessation
- 2012-11-23 WO PCT/EP2012/073426 patent/WO2013076227A1/de active Application Filing
- 2012-11-23 KR KR1020147017027A patent/KR20140098164A/ko not_active Application Discontinuation
- 2012-11-23 EP EP12788571.3A patent/EP2782904A1/de not_active Withdrawn
- 2012-11-23 AR ARP120104423A patent/AR088981A1/es active Pending
- 2012-11-23 EA EA201491031A patent/EA201491031A1/ru unknown
- 2012-11-23 TW TW101143851A patent/TW201328599A/zh unknown
- 2012-11-23 IN IN3823CHN2014 patent/IN2014CN03823A/en unknown
- 2012-11-23 US US14/360,437 patent/US9198429B2/en not_active Expired - Fee Related
- 2012-11-23 JP JP2014542840A patent/JP2015502933A/ja not_active Withdrawn
- 2012-11-23 CN CN201280068130.8A patent/CN104066725A/zh active Pending
- 2012-11-23 MX MX2014006073A patent/MX2014006073A/es unknown
-
2014
- 2014-05-23 CO CO14111769A patent/CO6970612A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US9198429B2 (en) | 2015-12-01 |
| IN2014CN03823A (ru) | 2015-10-16 |
| BR112014012588A2 (pt) | 2017-06-13 |
| WO2013076227A1 (de) | 2013-05-30 |
| CN104066725A (zh) | 2014-09-24 |
| JP2015502933A (ja) | 2015-01-29 |
| AR088981A1 (es) | 2014-07-23 |
| KR20140098164A (ko) | 2014-08-07 |
| MX2014006073A (es) | 2014-08-08 |
| EP2782904A1 (de) | 2014-10-01 |
| US20140274952A1 (en) | 2014-09-18 |
| EA201491031A1 (ru) | 2014-11-28 |
| TW201328599A (zh) | 2013-07-16 |
| CO6970612A2 (es) | 2014-06-13 |
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